tegafur
Conditions | Yield |
---|---|
With isopropyl alcohol at 75℃; for 4h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In tetrahydrofuran at 15 - 20℃; for 12h; Solvent; Reagent/catalyst; Temperature; | 99.8% |
Conditions | Yield |
---|---|
With bis(acetylacetonate)nickel(II); tris(2,2′-bipyridine)ruthenium(II) bis(tetrafluoroborate) In tetrahydrofuran at 25 - 30℃; Temperature; Solvent; Wavelength; Reagent/catalyst; Irradiation; | 98.7% |
With calcium chloride; trifluoroacetic acid In chloroform; N,N-dimethyl-formamide; toluene | 85.2% |
With dimethylmonochlorosilane; triethylamine In acetonitrile at 16℃; Temperature; | 85% |
Conditions | Yield |
---|---|
With sodium acetate; tetra-(n-butyl)ammonium iodide In dichloromethane; water at 35℃; for 2h; Solvent; Temperature; Reagent/catalyst; | 95.2% |
5-Fluoro-2,6-dioxo-3-(tetrahydro-furan-2-yl)-3,6-dihydro-2H-pyrimidine-1-carbothioic acid S-octyl ester
tegafur
Conditions | Yield |
---|---|
With isopropylamine In diethyl ether Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; copper diacetate In N,N-dimethyl-formamide at 40℃; for 5h; Reagent/catalyst; Time; Solvent; Temperature; | 92.35% |
With carbon tetrabromide; potassium carbonate In ethanol; water at 50 - 60℃; for 9.5h; Temperature; Reagent/catalyst; Inert atmosphere; | 82% |
With 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; caesium carbonate at 90℃; for 12h; Inert atmosphere; Sealed tube; | 39% |
2,3-dihydro-2H-furan
5-fluorouracil
dimethylsilicon dichloride
tegafur
Conditions | Yield |
---|---|
With sodium hydroxide; triethylamine In chloroform; acetonitrile | 85.5% |
With pyridine In acetonitrile | 75.4% |
5-fluoro-1-(2-tetrahydrofuryl)-6-hydroxy-5-methoxycarbonyl-5,6-dihydrouracil
tegafur
Conditions | Yield |
---|---|
With trifluoroacetic acid In water at 0℃; for 1104h; | 84% |
(4,4-Dimethoxy-butoxy)-trimethyl-silane
5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
tegafur
Conditions | Yield |
---|---|
With tin(IV) chloride In 1,2-dichloro-ethane; acetonitrile addition at 0 deg C, stirring at 23-25 deg C, 1h; | 84% |
2-chlorotetrahydrofuran
5-fluorouracil
A
tegafur
B
1,3-bis(tetrahydro-2-furyl)-5-fluorouracil
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide at 30℃; for 5h; | A 75% B 80% |
piperidine
tegafur
Conditions | Yield |
---|---|
With pyridine | 79.3% |
1,3-bis(tetrahydro-2-furyl)-5-fluorouracil
tegafur
Conditions | Yield |
---|---|
With water In ethanol at 50℃; for 2h; | 76% |
Conditions | Yield |
---|---|
Stage #1: 2-acetoxytetrahydrofuran; 5-fluorouracil With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 90℃; for 24h; Sealed tube; Stage #2: With water In ethanol at 70℃; for 1.5h; | 72% |
In N,N-dimethyl-formamide at 140℃; for 2h; | 53% |
With ammonium sulfate; cesium chloride; 1,1,1,3,3,3-hexamethyl-disilazane 2.) MeCN, 25 deg C, 3 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
In pyridine; chloroform; water | 72% |
2,3-dihydro-2H-furan
5-fluorouracil
A
tegafur
B
1,3-bis(tetrahydro-2-furyl)-5-fluorouracil
Conditions | Yield |
---|---|
With pyridine; phosphorus pentaoxide In chloroform | A 63% B n/a |
With 4-Methyl-1-benzolsulfonsaeure-trimethylsilylester In pyridine; 1,2-dichloro-ethane at 75 - 80℃; for 1h; | A 41% B n/a |
With pyridine hydrochloride In 1,2-dichloro-ethane at 75 - 80℃; Product distribution; other temperature, other solvents, other reagents; | A 1.73 g B n/a |
With pyridine In 1,2-dichloro-ethane at 75 - 80℃; Product distribution; other temperature, other solvents, other reagents; | A 1.73 g B n/a |
Conditions | Yield |
---|---|
In chloroform; N,N-dimethyl-formamide; acetone | 62.5% |
Conditions | Yield |
---|---|
In pyridine; chloroform; water | 58.3% |
2,3-dihydro-2H-furan
5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
tegafur
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In pyridine; 1,2-dichloro-ethane at 75 - 80℃; for 3h; | 51% |
2-acetoxytetrahydrofuran
5-fluorouracil
A
tegafur
B
5-fluoro-3-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
C
1,3-bis(tetrahydro-2-furyl)-5-fluorouracil
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 90℃; for 24h; Reagent/catalyst; Time; Sealed tube; | A 51% B 11% C 29% |
2,3-dihydro-2H-furan
5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
A
5-fluorouracil
B
tegafur
Conditions | Yield |
---|---|
With pyridine hydrochloride In chloroform at 60 - 70℃; Product distribution; other temperature, other solvents; | A 0.6 g B 44.5% |
2-acetoxytetrahydrofuran
5-fluorouracil
A
tegafur
B
1,3-bis(tetrahydro-2-furyl)-5-fluorouracil
Conditions | Yield |
---|---|
With ammonium sulfate; cesium chloride; 1,1,1,3,3,3-hexamethyl-disilazane 2.) MeCN, 25 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
2-acetoxytetrahydrofuran
A
tegafur
B
C8H8(2)HFN2O3
C
C8H7(2)H2FN2O3
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; Mechanism; isotopic effect; |
1-(2-tetrahydrofuryl)-5-methoxycarbonyluracil
A
5-fluorouracil
B
tegafur
Conditions | Yield |
---|---|
With sodium hydroxide; fluorine; acetic acid 1.) RT, 2.) H2O, 1 h, RT; Yield given. Multistep reaction; |
1-(2-tetrahydrofuryl)-5-methoxycarbonyluracil
tegafur
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 43 percent / F2/N2 (25percent) / H2O / Ambient temperature 2: 84 percent / CF3COOH / H2O / 1104 h / 0 °C View Scheme | |
With hydrogenchloride; sodium hydroxide; ammonia; potassium carbonate; sodium sulfate In methanol; water; acetic acid |
Conditions | Yield |
---|---|
In N-methyl-acetamide; chloroform |
Conditions | Yield |
---|---|
With tetramethlyammonium chloride In N-methyl-acetamide |
ammonium hydroxide
hypofluorous acid trifluoromethyl ester
1-(tetrahydro-furan-2-yl)-uracil
tegafur
Conditions | Yield |
---|---|
With nitrogen In methanol; dichloromethane |
Conditions | Yield |
---|---|
With ammonium hydroxide In tetrahydrofuran; methanol |
Conditions | Yield |
---|---|
tin(IV) chloride In 1,4-dioxane; chloroform; isopropyl alcohol |
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 20℃; for 18h; | 100% |
benzyl bromide
tegafur
3-(phenylmethyl)-1-(2-tetrahydrofuryl)-5-fluorouracil
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; acetone at 50 - 60℃; | 95% |
tegafur
trimethylsilylacetylene
1-(tetrahydrofuran-2-yl)-3-(m-nitrobenzyl)-5-fluorouracil
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 1h; Ambient temperature; | 95% |
chloro-methylsulfanyl-methane
tegafur
3-methylthiomethyl-1-(tetrahydro-2-furyl)-5-fluorouracil
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide 1.) 1 h, below 10 deg C, 2.) room temp., 8 h; | 93.9% |
Conditions | Yield |
---|---|
In ethanol; acetone at 50℃; for 8h; Solvent; Temperature; | 93.23% |
tegafur
5-(α-tegafur-m-nitro-p-tolyl)-10,15,20-triphenylporphyrin
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 10h; | 92.6% |
tegafur
2-chloro-ethanol
A
5-Fluoro-1,3-bis(2-hydroxyethyl)-uracil
B
N1-(2-furanidyl)-N3-(2-hydroxyethyl)-5-fluorouracil
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 80℃; for 6h; Title compound not separated from byproducts; | A n/a B 91% |
tegafur
1-(o-nitrobenzyl)-3-acetyl-5-fluorouracil
5-fluoro-3-(4-nitrobenzyl)-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 1h; Ambient temperature; | 90% |
tegafur
2-nitrophenylmethyl bromide
1-(tetrahydrofuran-2-yl)-3-(o-nitrobenzyl)-5-fluorouracil
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 1h; Ambient temperature; | 90% |
isonicotinamide
tegafur
Conditions | Yield |
---|---|
In methanol at 60℃; for 120h; | 88.23% |
p-methyloxycarbonylbenzyl chloride
tegafur
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 88% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; |
nicotinamide
tegafur
Conditions | Yield |
---|---|
In methanol at 60℃; for 120h; | 87.93% |
tegafur
2-hydroxyresorcinol
Conditions | Yield |
---|---|
In methanol for 0.5h; Milling; | 87.43% |
IUPAC Name: 5-Fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione
Synonyms of 5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7): 1-(2-Tetrahydrofuryl)-5-fluorouracil ; 1-(Tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedione ; 1-(Tetrahydrofuran-2-yl)-5-fluorouracil ; 2,4(1H,3H)Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)- ; 5-24-06-00285 (Beilstein Handbook Reference) ; 5-Fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedione ; 5-Fluoro-1-(tetrahydro-2-furyl)uracil ; 5-Fluoro-1-(tetrahydro-3-furyl)uracil ; 5-Fluoro-1-(tetrahydrofuran-2-yl)uracil ; BRN 0525766 ; CCRIS 2762 ; Citofur ; Coparogin ; EINECS 241-846-2 ; Exonal ; FT-207 ; Furafluor ; Furflucil ; Lamar ; Lifril ; MJF-12264 ; N(sub 1)-(2'-Furanidyl)-5-fluouracil ; N(sub 1)-(2'-Furanidyl)-5-fluouracil [Czech] ; N(sub 1)-(2-Tetrahydrofuryl)-5-fluorouracil ; N1-(2-tetrahydrofuryl)-5-fluorouracil ; NSC-148958 ; Neberk ; Nitobanil ; Phthorafur ; Phthorafur [Czech] ; Racemic Ftorafur ; Riol ; Sinoflurol ; Sunfral ; Tefsiel C ; Tegafur ; Tegafurum ; Tegafurum [INN-Latin] ; UNII-1548R74NSZ ; Uracil, 1-(tetrahydrofuran-2-yl)-5-fluoro- ; Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-
CAS NO: 17902-23-7
Classification Code: Antimetabolites ; Antimetabolites, antineoplastic ; Antineoplastic ; Antineoplastic Agents ; Drug / Therapeutic Agent ; Human Data ; Mutation data ; Noxae ; Reproductive Effect ; Tumor data
Molecular Formula: C8H9FN2O3
Molecular Weight: 200.1671
Molecular Structure:
Melting Point: 171-173 °C
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 49.85 Å2
Index of Refraction: 1.557
Molar Refractivity: 44.28 cm3
Molar Volume: 137.4 cm3
Surface Tension: 51.1 dyne/cm
Density of 5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7): 1.45 g/cm3
5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7) can be used as an antineoplastic
5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7) can be derived from condensation 5 - fluorouracil and 2 - acetoxy-tetrahydrofuran with the yield of the Act only about 15%.
Another production method is based on the synthesis of fluoride withthe starting material of 5 - fluorouracil, 6 methyl-2, and 3-methyl silicone alkyl ammonium chloride.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD50 | oral | 36mg/kg (36mg/kg) | BEHAVIORAL: TREMOR GASTROINTESTINAL: NAUSEA OR VOMITING | Journal of Pharmaceutical Sciences. Vol. 73, Pg. 212, 1984. |
dog | LD50 | oral | 34mg/kg (34mg/kg) | BEHAVIORAL: TREMOR VASCULAR: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING | Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 1009, 1980. |
human | LDLo | intravenous | 640mg/kg/8D (640mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION GASTROINTESTINAL: NAUSEA OR VOMITING | Cancer Vol. 36, Pg. 103, 1975. |
human | TDLo | intravenous | 23mg/kg (23mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Cancer Vol. 36, Pg. 103, 1975. |
man | TDLo | oral | 197mg/kg/23D- (197mg/kg) | BRAIN AND COVERINGS: ENCEPHALITIS BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: ANTIPSYCHOTIC | Internal Medicine. Vol. 31, Pg. 828, 1992. |
mouse | LD50 | intraperitoneal | 493mg/kg (493mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
mouse | LD50 | intravenous | 750mg/kg (750mg/kg) | United States Patent Document. Vol. #4130648, | |
mouse | LD50 | oral | 775mg/kg (775mg/kg) | Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 22, Pg. 27, 1987. | |
mouse | LD50 | subcutaneous | 760mg/kg (760mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 569, 1971. |
rabbit | LD50 | oral | 44mg/kg (44mg/kg) | VASCULAR: OTHER CHANGES | Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 1009, 1980. |
rabbit | LD50 | unreported | 40mg/kg (40mg/kg) | Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 7, Pg. 100, 1977. | |
rat | LD50 | intraperitoneal | 700mg/kg (700mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2911, 1978. |
rat | LD50 | intravenous | 685mg/kg (685mg/kg) | Gan to Kagaku Ryoho. Cancer and Chemotherapy. Vol. 10, Pg. 1987, 1983. | |
rat | LD50 | oral | 930mg/kg (930mg/kg) | GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2911, 1978. |
rat | LD50 | subcutaneous | 600mg/kg (600mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2911, 1978. |
Reported in EPA TSCA Inventory.
Poison by ingestion. Moderately toxic to humans by intravenous route. Moderately toxic experimentally by intraperitoneal, intravenous, and subcutaneous routes. Experimental teratogenic data. Human systemic effects: nausea and vomiting. Experimental reproductive effects. Questionable human carcinogen producing gastrointestinal tumors. Human mutation data reported. Used as an anti-cancer agent. When heated to decomposition it emits very toxic fumes of F− and NOx.
Safety Information of 5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7).
Hazard Codes: T
Risk Statements: 23/24/25
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36/37/39-45
S22: Do not breathe dust.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: YR0450000
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